DE1619437A1 - Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren - Google Patents
Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben PolymerenInfo
- Publication number
- DE1619437A1 DE1619437A1 DE19661619437 DE1619437A DE1619437A1 DE 1619437 A1 DE1619437 A1 DE 1619437A1 DE 19661619437 DE19661619437 DE 19661619437 DE 1619437 A DE1619437 A DE 1619437A DE 1619437 A1 DE1619437 A1 DE 1619437A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- amino
- radicals
- azo dyes
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000835 fiber Substances 0.000 title claims description 13
- 239000000987 azo dye Substances 0.000 title claims description 11
- 238000004043 dyeing Methods 0.000 title claims description 8
- 229920001600 hydrophobic polymer Polymers 0.000 title claims description 5
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- MENOBBYDZHOWLE-UHFFFAOYSA-N morpholine-2,3-dione Chemical compound O=C1NCCOC1=O MENOBBYDZHOWLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- JTHRRMFZHSDGNJ-UHFFFAOYSA-N piperazine-2,3-dione Chemical compound O=C1NCCNC1=O JTHRRMFZHSDGNJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims 2
- RSINTYZGAWHRBE-UHFFFAOYSA-N 1,3-thiazole-4,5-dione Chemical group O=C1SC=NC1=O RSINTYZGAWHRBE-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 229940035893 uracil Drugs 0.000 claims 1
- -1 2-benzothiazolyl radical Chemical group 0.000 description 58
- 150000003254 radicals Chemical class 0.000 description 32
- 239000000975 dye Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000004744 fabric Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 229920000728 polyester Polymers 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000003086 colorant Substances 0.000 description 4
- 229940091173 hydantoin Drugs 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- ZOBPZXTWZATXDG-UHFFFAOYSA-N 1,3-thiazolidine-2,4-dione Chemical group O=C1CSC(=O)N1 ZOBPZXTWZATXDG-UHFFFAOYSA-N 0.000 description 2
- GDFCZZHSWGWCHP-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-6-carbonitrile Chemical compound C1=C(C#N)C=C2SC(N)=NC2=C1 GDFCZZHSWGWCHP-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical class C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 2
- ZYHNHJAMVNINSY-UHFFFAOYSA-N 6-methylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 ZYHNHJAMVNINSY-UHFFFAOYSA-N 0.000 description 2
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229940123464 Thiazolidinedione Drugs 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- FVNSRFMQXKMHTQ-UHFFFAOYSA-N (2-amino-1,3-benzothiazol-6-yl) thiocyanate Chemical compound C1=C(SC#N)C=C2SC(N)=NC2=C1 FVNSRFMQXKMHTQ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- KJRDZJGBIBLGKB-UHFFFAOYSA-N 5,6-dimethoxy-1,3-benzothiazol-2-amine Chemical compound C1=C(OC)C(OC)=CC2=C1SC(N)=N2 KJRDZJGBIBLGKB-UHFFFAOYSA-N 0.000 description 1
- OMIHQJBWAPWLBO-UHFFFAOYSA-N 5-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2SC(N)=NC2=C1 OMIHQJBWAPWLBO-UHFFFAOYSA-N 0.000 description 1
- UZJMSFZHPMSAHI-UHFFFAOYSA-N 6-butoxy-1,3-benzothiazol-2-amine Chemical compound CCCCOC1=CC=C2N=C(N)SC2=C1 UZJMSFZHPMSAHI-UHFFFAOYSA-N 0.000 description 1
- GFGBNISGCXRRGF-UHFFFAOYSA-N 6-butyl-1,3-benzothiazol-2-amine Chemical compound CCCCC1=CC=C2N=C(N)SC2=C1 GFGBNISGCXRRGF-UHFFFAOYSA-N 0.000 description 1
- FTSHQQBFLIGSPW-UHFFFAOYSA-N 6-butylsulfonyl-1,3-benzothiazol-2-amine Chemical compound NC=1SC2=C(N1)C=CC(=C2)S(=O)(=O)CCCC FTSHQQBFLIGSPW-UHFFFAOYSA-N 0.000 description 1
- VMNXKIDUTPOHPO-UHFFFAOYSA-N 6-chloro-1,3-benzothiazol-2-amine Chemical compound C1=C(Cl)C=C2SC(N)=NC2=C1 VMNXKIDUTPOHPO-UHFFFAOYSA-N 0.000 description 1
- KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 description 1
- XSDOQGXRBLPHHU-UHFFFAOYSA-N 6-ethyl-1,3-benzothiazol-2-amine Chemical compound CCC1=CC=C2N=C(N)SC2=C1 XSDOQGXRBLPHHU-UHFFFAOYSA-N 0.000 description 1
- KPTLRIXDAQTXCU-UHFFFAOYSA-N 6-ethylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CCS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 KPTLRIXDAQTXCU-UHFFFAOYSA-N 0.000 description 1
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
- DZWTXWPRWRLHIL-UHFFFAOYSA-N 6-methyl-1,3-benzothiazol-2-amine Chemical compound CC1=CC=C2N=C(N)SC2=C1 DZWTXWPRWRLHIL-UHFFFAOYSA-N 0.000 description 1
- QJWBDYBQSKYQKM-UHFFFAOYSA-N 6-propoxy-1,3-benzothiazol-2-amine Chemical compound CCCOC1=CC=C2N=C(N)SC2=C1 QJWBDYBQSKYQKM-UHFFFAOYSA-N 0.000 description 1
- LBOPQKGVJMWWEA-UHFFFAOYSA-N 6-propyl-1,3-benzothiazol-2-amine Chemical compound CCCC1=CC=C2N=C(N)SC2=C1 LBOPQKGVJMWWEA-UHFFFAOYSA-N 0.000 description 1
- BZRZTBIBTJSVHY-UHFFFAOYSA-N 6-propylsulfonyl-1,3-benzothiazol-2-amine Chemical compound CCCS(=O)(=O)C1=CC=C2N=C(N)SC2=C1 BZRZTBIBTJSVHY-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical group COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- DXYYSGDWQCSKKO-UHFFFAOYSA-N methylbenzothiazole Natural products C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 1
- MXAJVDHGJCYEKL-UHFFFAOYSA-N morpholine-3,5-dione Chemical compound O=C1COCC(=O)N1 MXAJVDHGJCYEKL-UHFFFAOYSA-N 0.000 description 1
- GUYMMHOQXYZMJQ-UHFFFAOYSA-N n-ethyl-3-methylaniline Chemical compound CCNC1=CC=CC(C)=C1 GUYMMHOQXYZMJQ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- AUPJTDWZPFFCCP-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCCN(C)CCS([O-])(=O)=O AUPJTDWZPFFCCP-GMFCBQQYSA-M 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49613065A | 1965-10-14 | 1965-10-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1619437A1 true DE1619437A1 (de) | 1969-10-23 |
Family
ID=23971360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661619437 Pending DE1619437A1 (de) | 1965-10-14 | 1966-10-13 | Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3423394A (enrdf_load_stackoverflow) |
| BE (1) | BE687587A (enrdf_load_stackoverflow) |
| CH (1) | CH466461A (enrdf_load_stackoverflow) |
| DE (1) | DE1619437A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1163831A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4123538A (en) * | 1977-08-30 | 1978-10-31 | Mcneil Laboratories, Incorporated | (2-Amino-2-oxoethoxy)acetic acid compounds, compositions and methods |
| US5879444A (en) * | 1997-09-02 | 1999-03-09 | Bayer Corporation | Organic pigment compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3161631A (en) * | 1962-10-22 | 1964-12-15 | Eastman Kodak Co | Benzothiazole azo compounds containing a dicarboximido radical |
-
1965
- 1965-10-14 US US496130A patent/US3423394A/en not_active Expired - Lifetime
-
1966
- 1966-09-15 GB GB41189/66A patent/GB1163831A/en not_active Expired
- 1966-09-29 BE BE687587D patent/BE687587A/xx unknown
- 1966-10-11 CH CH1472466A patent/CH466461A/fr unknown
- 1966-10-13 DE DE19661619437 patent/DE1619437A1/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH466461A (fr) | 1968-12-15 |
| BE687587A (enrdf_load_stackoverflow) | 1967-03-01 |
| US3423394A (en) | 1969-01-21 |
| GB1163831A (en) | 1969-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1619428A1 (de) | Verwendung von quaternaeren Methinverbindungen zum Faerben von Textilgut aus Faeden oder Fasern aus hydrophoben Polymeren | |
| DE1769423A1 (de) | Neue Disazoverbindungen,Verfahren zu deren Herstellung und Anwendung | |
| DE1619437A1 (de) | Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren | |
| DE1644325A1 (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE3313797A1 (de) | Monoazofarbstoffe zum faerben von polyesterfasern | |
| DE1769025A1 (de) | Monoazofarbstoffe | |
| DE1469868C3 (de) | Verwendung von heterocyclischen Farbstoffen zum Färben von Polyamiden in der Masse | |
| DE2364476B2 (de) | Dispersionsmonoazofarbstoffe und ihre Verwendung | |
| DE1619418A1 (de) | Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren | |
| DE1769323A1 (de) | Monoazofarbstoffe | |
| DE2608020A1 (de) | Naphthostyrilfarbstoffe | |
| US3370055A (en) | Thiazolylazophenyl dyes containign dicarboximido radicals | |
| DE1802863B1 (de) | Verwendung von sulfonsaeuregruppenhaltigen Farbstoffen zum Faerben von Textilmaterial aus Polyamiden | |
| DE2357442C3 (de) | Naphtholactamfarbstoffe und deren Verwendung | |
| DE2205062A1 (de) | Neue, wasserunloesliche azofarbstoffe und verfahren zu ihrer herstellung | |
| DE2724566A1 (de) | Naphtholaktam-farbstoffe | |
| DE1469688A1 (de) | Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren | |
| DE2824710A1 (de) | Wasserunloesliche monoazofarbstoffe | |
| DE2305984A1 (de) | Neue azo-pyrazolium-farbstoffe, verfahren zu ihrer herstellung und ihre verwendung | |
| EP0057418B1 (de) | Präparationen von Nitro-anilinen | |
| DE2711130C2 (de) | Azofarbstoffe | |
| DE2212755A1 (de) | Wasserunloesliche monoazofarbstoffe und verfahren zu ihrer herstellung | |
| DE1619435A1 (de) | Verwendung von Azofarbstoffen zum Faerben von Faeden und Fasern aus hydrophoben Polymeren | |
| DE2724541A1 (de) | Naphtholaktam-farbstoffe | |
| DE1644142A1 (de) | Verfahren zur Herstellung von Azofarbstoffen |